Phosphorus oxychloride → 3-Chloromethyl-1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine
Reaction equation
P(Cl)(Cl)([Cl:3])=O.[O:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:7]1[CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH2:24]O)([CH3:23])[CH2:18]1>>[Cl:3][CH2:24][C:19]1([CH3:23])[CH2:20][CH2:21][CH2:22][N:17]([CH2:16][CH:7]2[O:6][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH2:18]1Participants
3
Procedure
A mixture of phosphorus oxychloride (1.93 ml, 0.02 mmol) and [1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]methanol (0.2 g, 0.72 mmol) was refluxed for 3 h. Excess of phosphorus oxychloride was evaporated. Water was slowly added and the reaction mixture was made alkaline with aq NaOH and extracted with DCM (3×5 ml). The combined organic phases were dried over Na2SO4, filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (DCM/MeOH, 90:10).
Workup
- temperature